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The Thursday guilty plea of former Trump Organization Chief Financial Officer Allen Weisselberg is the latest and largest development in New York officials’ multiyear investigation into the company headed by the former president.
Weisselberg pleaded guilty to 15 counts related to tax fraud and will serve five months in prison followed by five years of probation. He will also pay almost $2 million in back taxes and penalties.
As part of his agreement with the Manhattan District Attorney’s office, Weisselberg admitted to playing a role in enriching himself and other top Trump Organization executives through off-the-books benefits and other measures without reporting the income. He personally avoided paying $1.7 million in taxes over more than a decade through indirect compensation from the Trump Organization.
The case against the Trump Organization itself is set to begin jury selection in October, and Weisselberg will testify in the case.
Legal experts said Weisselberg may not have officially agreed to cooperate, but his testimony could still be valuable to the prosecution advancing its case that the Trump Organization committed financial misdeeds.
Andrew Weissmann, a professor of practice at New York University School of Law, said the stipulation that Weisselberg must testify truthfully for his deal to remain intact makes it “much harder” for the Trump Organization to defend itself in its case.
“The organization acts through its people,” he said. “This is the CFO saying that he did this and these are not crimes that are unrelated to the organization and the organization benefited directly from this.”
Weissmann, who served as a lead prosecutor for special counsel Robert Mueller’s office in his investigation into Russian interference in the 2016 presidential election, said Weisselberg fully cooperating would mean he would have to provide all information he knows about other crimes, including those unrelated to what he and the organization have been charged with.
Former Manhattan District Attorney Cyrus Vance originally charged Weisselberg and the Trump Organization at the same time a year ago. Alvin Bragg took over the case when he became district attorney at the start of this year.
Trump himself has not been charged with any crime, though prosecutors have not ruled it out.
Weissmann said Weisselberg “essentially” is cooperating with the investigation with respect to this specific case because he will need to take the stand and answer questions about the charges he pleaded guilty to.
He said the defense was able to cap Weisselberg’s exposure in accepting the deal, preventing him from facing a possibly steeper sentence. He said the sentence could have been the same if Weisselberg went through a trial and was convicted, but determining what he would have received is difficult to predict in such a high-profile case.
Weissmann said Weisselberg pleading guilty to every count of the indictment facing him is a significant win for the prosecution.
Danya Perry, a former federal prosecutor, said the Trump Organization’s defense team may try to argue in its case that Weisselberg is motivated to testify against the company, but him receiving a five-month sentence and not fully cooperating makes that a more complicated argument.
She said she does not think Weisselberg would have faced an “incredibly” stiff sentence if convicted due to his age — 75 — and being a first-time offender.
Perry said if the case against the organization goes to trial, the former president’s name will come up often, and it would be difficult to “thread the needle” that the organization was involved in financial misdeeds but he wasn’t.
She said if the firm enters into a plea agreement, that may be as far as the district attorney’s case goes, but it is unclear what information may come out in a trial.
“If there’s a trial and Weisselberg testifies, who knows what other information will come out?” Perry asked.
Weissmann and Perry both said they were interested in the fact that Weisselberg was not granted full immunity for any other potential crimes.
“Typically, lawyers negotiate for coverage or immunity for any other crimes he might have committed so they can’t keep coming back,” Perry said. “Here, they didn’t do that.”
Weissmann said defense counsels requesting coverage in a plea agreement for other crimes that may have been committed is “standard,” so someone knows “there’s nothing waiting in the wings.”
He said its exclusion from the agreement is “striking” and makes him believe Bragg more when he said the investigation is ongoing.
“That made me think that we all need to sort of take a deep breath and wait to see what happens after the Trump Organization trial, and so whether other charges get brought,” Weissmann said.
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